Triethylamine → 2-ethoxy-N-(6-methyl-2-phenoxy-4-{2-[3-(pyridin-3-yl)propoxy]ethylamino}pyridin-3-yl)acetamide
Reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([NH2:15])=[C:4]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:3]=1.C(N(CC)CC)C.[CH2:36]([O:38][CH2:39][C:40](Cl)=[O:41])[CH3:37]>ClCCl>[CH2:36]([O:38][CH2:39][C:40]([NH:15][C:5]1[C:6]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:7][C:2]([CH3:1])=[CH:3][C:4]=1[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:41])[CH3:37]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere, a solution of 6-methyl-2-phenoxy-N4-{2-[3-(pyridin-3-yl)propoxy]ethyl}pyridine-3,4-diamine (5.2 g, 14 mmol), anhydrous dichloromethane (40 mL), and anhydrous triethylamine (2.3 mL, 16.5 mmol) was cooled to 5° C. A solution of ethoxyacetyl chloride (1.77 g, 14.4 mmol) in dichloromethane (10 mL) was then added over a period of ten minutes, and the reaction was stirred for 30 minutes. The reaction mixture was diluted with dichloromethane (25 mL), washed with aqueous saturated sodium bicarbonate (3×) and brine (3×), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 5.8 g of 2-ethoxy-N-(6-methyl-2-phenoxy-4-{2-[3-(pyridin-3-yl)propoxy]ethylamino}pyridin-3-yl)acetamide as an oil.
Workup
- washwashed with aqueous saturated sodium bicarbonate (3×) and brine (3×)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5770e1f215f34cc6ba8c54c93a5f503d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125890B2
Reaction notes
Loading…